Clarke (1919-1997) was a pioneering figure in American indie film. Her two fiction features preceding “Portrait, “The Connection” (1962) and “The Cool World” (1963), both deal with race and marginality, as does “Portrait.”

The untrustworthiness of the tale has to do with Clarke’s approach. She’ll let the camera go out of focus or the screen go black as Holliday continues to talk. It’s an arty, ’60s touch that feels dated. Worse, she allows a couple of people off-screen to hector Holliday. Clarke was as genuinely hip a filmmaker as there was in America back then. Yet her fascination with Holliday increasingly reveals itself as owing more to revulsion, even condemnation, than appreciation.

The documentary was shot over the course of one very long night in Clarke’s digs in the Chelsea Hotel. She had one of two penthouse apartments there. Virgil Thomson had the other. Truly, it was a different world then.

Holliday (born Aaron Payne, in 1924) looks very dap in his George Burns glasses, open-neck dress shirt, and double-breasted blazer. He briefly puts on a feather boa, too (doing a “Carmen Jones” riff). Usually, he holds a cigarette, a cocktail, or joint — suitable props for his high-gloss, low-life style. Yes, he’s black. Yes, he’s a guy. But in an ideal world, Holliday, not Audrey Hepburn, would have been Holly Golightly in “Breakfast at Tiffany’s.”

“If I’d been a ranch,” Holliday says, “they’d have named me the Bar None.” He comes across as a louche Bobby Short or unlettered James Baldwin: that same kind of style, that same kind of self-dramatizing flair. “I’m a stone whore,” Holliday laughs, “and I’m not ashamed of it.” His bespoke shamelessness is pretty irresistible. He tells stories from his past: about a father who beat him, a San Francisco sugar daddy whose house he cleaned out, his affection for amyl nitrate poppers. He does a knockout a cappella version of a Fanny Brice song, as well as imitations of Mae West (not very good), Miles Davis (dead on), Butterfly McQueen (ditto), Pearl Bailey (OK), Katharine Hepburn (the “calla lilies” speech, from “Stage Door,” what else?). A lot of this is shtick, but it’s shtick he’s made so thoroughly his own that it comes across as something more: a kind of identity.

“I go out of my way to unglue people,” Holliday cheerily confesses early on. It’s as much boast as admission. A few times during the documentary, he’s the unglued one: collapsing with laughter while smoking that joint, asking forgiveness from one of the unseen voices off-screen. Most startling of all, about midway through the documentary, Clarke has a long, silent close-up of Holliday’s face in repose. The blankness of expression couldn’t be more incongruous. Jason Holliday minus animation can’t be Jason Holliday. But then who is he? Only Aaron Payne knows, and probably not even him.

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